Trimethylsilylacetylene → 2-[4-[2-(Trimethylsilyl)ethynyl]phenyl]pyridine

HRID 1522713ノート

反応式

HRID 1522713 の反応式
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].I[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:1][Si:2]([C:5]#[C:6][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:12][CH:13]=1)([CH3:4])[CH3:3]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 69237907HCID 69237907、化合物

生成物 1

HCID 692372572-[4-[2-(Trimethylsilyl)ethynyl]phenyl]pyridine収率 72%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

実験手順

Trimethylsilylacetylene (4.1 mL, 28.8 mmol) and tetrakis(triphenylphosphine)palladium (0) (832 mg, 0.72 mmol) were added to a suspension of (1) (4.06 g, 14.4 mmol) and copper (I) iodide (274 mg, 1.44 mmol) in triethylamine (120 mL) that had been deoxygenated with argon. The mixture was deoxygenated with argon and then stirred under argon at room temperature for 40 hours. Aqueous hydrochloric acid (3 M, 320 mL) and dichloromethane (250 mL) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with aqueous hydrochloric acid (3 M, 30 mL), water (250 mL), brine (250 mL), dried over anhydrous magnesium sulfate, filtered and then the solvent was completely removed. The residue was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:4) as the eluent. The main band was isolated and the solvent completely removed to give (2) (2.59 g, 72%).

後処理

  1. customhad been deoxygenated with argon
  2. customThe mixture was deoxygenated with argon
  3. additionAqueous hydrochloric acid (3 M, 320 mL) and dichloromethane (250 mL) were added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
  6. washThe combined organic layers were washed with aqueous hydrochloric acid (3 M, 30 mL), water (250 mL), brine (250 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was completely removed
  10. customThe residue was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:4) as the eluent
  11. customThe main band was isolated
  12. customthe solvent completely removed

出典と根拠

ORDレコード
ord-1fbf2dd3245e487599b5e80e6bca2a02
出典データセット
uspto-grants-2015_07
特許番号
US09078330B2

反応ノート

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